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Regulatory regimes are notoriously resistant to change, so when less powerful actors manage to reshape long-established rules and gain increased access to a natural resource the interesting question is why? This article investigates relations between different claimant groups and the state in the reshaping of the regulations governing Oregon's private forestlands, how this process was mediated by broader political opportunities and constraints, and the conditions that supported a shift in the legal regime that benefited less advantaged interests. The intent is to deepen our understanding of the circumstances under which well-established rules of governance are altered. Analysis points to each of the following variables as significant for successful reform: (1) active challengers and their success in reframing issues to support their goals, (2) new political opportunities facilitating wider participation in the rulemaking process, and (3) concurrence between local and national aspirations supporting reform. While each condition is noteworthy, it is insufficient on its own. Rather, my study comparing two contested administrative rules suggests that a clear alignment of all three variables provides the strongest impetus for legislative and administrative rule changes at the state level benefiting less advantaged interests.